(Halloween party truth or dare)
*reader has plot of Elena
Warnings: 18+, slightly rough
months since (y/n) had been touched by a man. Her last intimate moment had been a gentle kiss with the person she swore she would never willingly touch. But things change and she would have never forgiven herself if she let Damon die without showing him how much she cared. She was prepared to grieve the man who had gotten under her skin, against her best efforts. She had realized a part of her would die with him.
Along with that part would be the guilt she carried. The way she would get excited when he would walk into a room. The sick feeling knowing she could easily have him if she just asked and how sometimes she fantasized about what he would do to her when she finally gave in. That didn’t compare to the worst of her crimes. There were times she had made sure Damon would hear her moans and cries as Stefan thrusted into her.
“Please harder,” she would beg her voice echoing throughout the boarding house. Always one to please Stefan did as he was asked. He didn’t care if Damon heard. He wanted him to know (y/n) was his and that he would never be able to experience the heaven that was being inside of her. If only he had known she screamed and begged hoping his brother was listening. Sometimes she even imagined Damon with flushed cheeks, his need for her burning through him like a fire he couldn’t put out. She would imagine him with his head thrown back and his eyes shut tightly as he stroked himself pretending he was the one responsible for her pleasure.
She would shriek “ Oh my god, please, I’m gonna cum,” when her fantasy had gotten her to her peak and even louder and raspier “ I want you to cum with me!” Her (y/e/c) eyes would slam shut as she thought of Damon stroking his cock faster and being pushed over the edge with her. Self hatred would wash over her afterwards knowing she betrayed Stefan but no one but her would ever know.
(Y/n) couldn’t help but feel some relief knowing the man she truly wanted could no longer plague her relationship or mind. Though as soon as her mirror image walked into his room with with a crimson colored bottle that was the cure, (y/n) felt more relived then she ever had in her life. That relief soon ended when Katherine happily announced that Stefan had given himself to Klaus to save his brother.
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It was a cool fall day in Mystic falls. Four months after stefan left and made it clear he was not coming back. Damon Salvatore sat on his leather sofa reading from dust returned by ray Bradbury getting himself thoroughly into the fall spirit. His favorite time of year. The sound of the crackling fire place and smell of leaves falling outside was the perfect combination for relaxation.
“ Damon! Why aren’t you answering my calls I’ve been trying to reach you for hours?,” Carloline Forbes voice boomed, the door slamming shut behind her.
He looked at her pointedly “ Well maybe I put my phone on silent so I could have a relaxing day without someone needing my help for a mundane task any human could fufill.”
Caroline huffed, “ this is a big deal Damon, Tyler’s mom has the flu so now we don’t have a place for our yearly friend-o- ween party!”
Damon Laughed, “ friend-o-ween? That’s the best you guys could come up with?”
“ We made it up in middle school and it’s cute!,” she argued. “ please Damon no one else can have it at their house.”
Caroline shrieked and jumped “yay! I’ll go get all the decorations!”
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What was supposed to be a relaxing day turned into hours of assisting Caroline in decorating the boarding house until it looked like something out of a movie. The lighting was dim. Orange and purple lights were strung throughout the house giving it a spooky yet enchanting glow. There were real pumpkins, fake pumpkins, spider webs, skeletons and other spooky decorations. It really was overkill but he did have to admit he enjoyed the finished result.
They stood finally finished Caroline grinning. “ This looks amazing. Oh! I forgot about the food! I’ll have Matt bring the snacks by before everyone else gets here. I have to start getting ready. I’m running behind! You better have a costume Damon!” She said so quickly it’d be hard to understand if he wasn’t supernatural. She left slamming the door behind her.
With an hour to go Damon walked upstairs deciding to take a shower before the party. He stripped his clothes and turned the shower on high heat enjoying the steam that filled up his large room. He decided he would just splash some fake blood on himself as a costume and his mind began to wander to (y/n) wondering what she might wear. He liked her sexy nurse costume but it probably had too many negative emotions attached to it after the last time she wore it. Damon felt guilty over what had happened but all he could think about right now was how badly he had wanted her that night. He could have thrown her in a school bus and fucked her for hours he had been so worked up from her anger towards him. His cock got hard at the thought and he moved his hand down his chiseled wet abs and gripped it.
He started to stroke it thinking of what he normally did, memories of (y/n) moaning and cumming. He should feel ashamed or grossed out by the fact it was because his brother was fucking her but he didn’t care. He could easily remember those sounds and pretend they were caused by him. He stroked himself even faster imagining the school bus fantasy. His arm supported him against the glass wall as the other twisted and began to stroke himself faster. He was so close he was going to
“Damon!,” Matt’s voice yelled from downstairs and Damon had never wanted to kill Matt more than in that moment. He lost the coiling feeling in his abdomen and shut the water off quickly. Pissed he quickly threw on pants and a white v neck.
Once downstairs he helped Matt set out all of the food besides the pizzas Caroline was ordering. If only he had showed up one minute later, Damon thought still extremely frustrated. He splattered some fake blood on his white shirt and face. Then put Caroline’s cheesy Halloween music on that she said he HAD to play.
The door opened and he got excited hoping it was (y/n) but to his disappointment blondie appeared with Tyler and witchy. Bonnie wore a black latex bodysuit with cat ears and Caroline was wearing a black lingerie nighty with animal ears as well. “ I see you decide to go as a slutty hamster,” he joked confused by her outfit.
“ I’m a mouse duh,” she said pointing to her ears the reference lost on him.
Bonnie looked at Tyler in his football jersey and Damon in “ blood” splattered . “ I see you two put in a lot of effort,” she joked.
“ if you want me to take it all off all you had to do was ask bon bon,” Damon joked back as she rolled her eyes.
Everyone moved to the kitchen snacking on chips and soda waiting for the pizza to arrive while Damon anxiously waited for (y/n) . The pizza delivery guy arrived before her much to his dismay and Caroline seeing the look on his face added “ It’ll be worth the wait Damon,” as she smiled. He ignored her not knowing what she meant and poured himself a bourbon as they all sat around eating pizza. When the door finally opened Jeremy came in first wearing a black hoodie as usual (y/n) following behind him.
Damon’s eyes bulged and he tried to stop another area from doing the same as he saw her costume. She was dressed like a playboy bunny and it was the least clothed he had ever seen her. Now he really was hating Matt because tonight was going to be torture until he could relieve himself.
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A few hours later they all sat in a circle on the floor in front of the crackling fireplace, filled shot glasses in front of each of them as Caroline yelled. “ Okay never have I ever, so if you have take a shot! Also no lying.” “ I’ll go first! Never have I ever had a one night stand.” Damon and Tyler took a shot.
Bonnie went next, “ never have I ever kissed a girl.” Everyone took a shot besides Bonnie and learning this new fact about (y/n) was making it even harder on him. Especially since he was trying not to stare all night as is.
Tyler went next “ never have I ever slept with Damon Salvatore,” laughing as Caroline hit him and took a shot.
Matt went next following Tyler’s lead , “ never have I ever fantasized about Damon Salvatore.” Also looking at Caroline. She took a shot.
“ Wow I’m hurt Matt,” Damon joked and noticed out of the corner of his eye (y/n) taking a shot too. He thought he could explode right then. He clapped his hands getting everyone’s attention . “Alright this is dumb, lets do truth or dare, you know there’s nothing I won’t do.” He winked. Since it’s my turn I’ll go first he turned to (y/n) whose heartbeat immediately increased.
“ (y/n) ,” he said slowly. “ truth or dare?”
She figured he saw that she had taken a shot for fantasizing about him and knew he would probably ask about that so in this case dare was the safe option. “ dare.”
Damon smirked, “ I dare you to tell me what you fantasized about me doing.” Her face went red.
“ That’s not how it works Damon it has to be an actual dare,” Bonnie said trying to cock block him like usual.
“ Fine,” he looked at (y/n) who was still flushed “ Then I dare you to kiss Caroline.”
(Y/n) crawled over to Caroline on her hands and knees seductively. Her pink body suit showing off her ass with a cute little bunny tail on it. She sat in front of her moving her blonde curled hair behind her ear and passionately kissed her. Caroline wrapped her hands into (y/n)s hair as they moaned into each other mouths. They pulled away laughing and at this point all the men were slightly hard. Even Jeremy, though he would never admit it. (Y/n) crawled back to her spot next to Damon and glared at him. Worried what his dare would be after that so he picked truth.
She acted like she was thinking it over “ have you ever jerked off while thinking about me Damon?” She asked trying to embarrass him, making everyone but Caroline slightly uncomfortable. Only because she knew (y/n) and Damon just needed to bang it out already.
He kept eye contact, “ right before everyone got here I was thinking about you in your sexy little nurse costume. Oh by the way Matt thanks for interrupting right as I was about to cum.”
His answer was followed by some a few ewww’s and Jeremy, Bonnie and Matt deciding it was time to go. Now it was Caroline’s turn and she was playing matchmaker “ (y/n) truth or dare,”
“ truth,” she responded nervous yet excited.
“ what is your naughtiest fantasy of Damon?”
(Y/n) froze debating on lying but new the supernaturals would easily be able to tell. Looking down ashamed she responded quietly, “ that he would jerk off while hearing stefan and I ... well you know.”
Damon couldn’t believe it. It wasn’t always stefan after all. Had she wanted him the entire time? Did this mean she was purposefully being loud? Was she always thinking about him when her and his baby bro did the deed?
Tyler interrupted his thoughts. “ Caroline truth or dare ?” He said quickly trying to move things away from (y/n) who was obviously embarrassed.
Caroline’s face lit up, “dare.”
“ I dare you to kiss me.” Caroline moved over to him getting into his lap kissing him their bodies pressing close together as Damon and (y/n) looked at each other awkwardly. Caroline let out a small moan and Damon coughed loudly trying to remind them they weren’t alone.
Feeling turned on from so many of the events that happened today and now knowing how long (y/n) had been wanting him physically Damon looked over to her yet again. “ truth or dare ?”
Her face was flushed from Tyler and Caroline’s show of affection and it reminded her how badly she needed intimacy. Damon was sexy all the time but now with his tousled hair and blood spattered shirt he looked rough and it was making her think about all the times he had gotten bloody to save her. How strong and rough he actually was. She wanted to be closer to him she hoped choosing dare would grant that wish. “Dare.”
He patted his lap “ come sit.” She crawled over to him and took a seat in his lap her back facing his chest and his arms wrapped around her tightly. She could feel the buldge underneath his Jeans and her core tightned feeling him pressed against her. He ran his nose along the inside of her neck and whispered “ your turn.”
She responded the need for him finally taking over. “ truth or dare Damon” she said in a husky tone her face turned towards him looking into his eyes, her need evident.
“ kiss me,” she dared and without hesitation Damon pulled her face to his forcefully. They moaned into each other’s mouths and Damon wrapped an arm around her and the other in her hair after throwing her bunny ears off of her. Well aware of what was about to happen and in need of release themselves Caroline and Tyler snuck out unnoticed.
Damon pushed (y/n) unto her back hovering above her, their lips always connected. He pressed her body firmly into the floor grinding into her core enjoying as she bucked her hips up to meet his. He moved his mouth to her neck kissing it aggressively. “ I want you so fucking bad (y/n) ,” She trembled underneath him.
“ please Damon.” With that he sat back and ripped off her tiny pink body suit leaving her in a black bra and panty set. She sat up and kissed him pulling away to lift his shirt over his head. He picked her up easily sitting her on the leather couch closer to the lit fireplace. He stood in front of her and she fumbled slightly trying to get his pants off as quick as she could. Her eyes widened when she unzipped his black jeans and realized he was going commando and he was BIG. His large erection sprung out of his pants standing proudly in front of her face. He stepped out of his pants and was going to resume undressing (y/n) but that thought was forgotten about when she wrapped her hand around him and did and experimental tug.
She looked up at him her (y/e/c) eyes meeting his blue as she stuck her tongue out and slowly licked his tip a few times before wrapping her lips around him completely.
“ fuck (y/n) ,” he moaned as she went further down on him, bobbing her head up and down on his length. She began to use her hand stroking what couldn’t fit in her mouth. Damon wrapped his hand around her throat gently pushing her off of him knowing If she continued he wouldn’t last much longer. Using his grip on her throat he pushed her back into the couch and crawled untop of her kissing her passionately. His other hand reached being her back unclasping her bra and she gasped as the cool air hit the newly exposed skin. He began to kiss down her neck his fingers traveling to play with her over her soaked panties. “ so wet.” He moaned against her neck as she began to grind into his hand.
Damon moved lower sucking her nipple into his mouth gently nibbling on it as he slipped his hand underneath her underwear making direct contact with her clit. “Please Damon, I need you inside me,” she cried desperately wanting him more than she thought was humanly possible.
He lifted his head from her breast looking down at her. The need evident in her eyes and ripped her panties off of her. Hovering over top of her he grabbed his member and and ran it along her folds watching as her wetness coated him. Looking down at her biting her lip he asked , “ are you sure you want this?”
“ I’ll always want you Damon,” she replied the sincerity clear on her face. With that Damon slowly guided his head into her. He watched her face as she slightly winced and leaned down to kiss her softly. He moved back and slowly slid farther into her. He kissed the side of her face gently trying to remind himself she hadn’t had sex in months and stefan wasn’t as well endowed as he was. Her tightness was testing his will power but he didn’t want to hurt her.
“ are you doing okay?,” he asked moving his hand down to her clit softly rubbing her knowing it would help her adjust more easily.
She moaned her eyes shut tightly the feeling of him stretching her so far. “ yes,” she lifted her hips trying to show him she wanted more , “ I want all of you Damon.” With that he pulled almost all of her heat and thrusted back in completely connecting them.
“ yes!” She cried out feeling like they were made for each other. He pulled back again and thrust in slow and deep enjoying the look of pleasure on her face. He continued his slow thrusts rolling his hips into her filling her all the way. He sat back and watched as her folds gripped him tightly. The view bringing him closer to his release. Damon sped up his pace slightly pulling out mostly than thrusting back into her using more force than before. He could feel her pussy begin to tighten around him and moved to rest his forehead against hers.
“ I want you to come for me (y/n). ” He sped up his circles on her clit and thrust into her harder and harder his abs tensing trying to hold off his orgasm.
(Y/n) began to tremble underneath him, “ I’m close!” she exclaimed. Her legs began shaking uncontrollably the pleasure like nothing she had ever experienced before.
“ me too ,” he grunted on the edge “ I want you to come with me.” He thrust again softly whispering “ come on baby, come on my cock for me.” Feeling her walls start to pulse around him.
With that she cried “ yes! I’m cumming, Damon yes!”
“ Fuck (y/n) ,” he growled, her walls gripping him harder pulling his orgasm from him as he continued to move inside of her.
They lay there still connected the aftershocks traveling through their bodies. He kissed her before slowly pulling out and rolling off the couch onto the soft carpet in front of the fire place. He patted next to him. “ join me?”
She slowly moved beside him her muscles already sore from her incredible orgasm. He played with her hair as she asked him “ truth or dare?”
“ truth,” he responded not questioning her motive.
“ I always have (y/n),” he paused “ do you love me?”
“ yes, I always will .” With that he brought her mouth to his sealing their love with that one special kiss.
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